4-Chlorobenzenesulfonyl chloride → Ethyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate

HRID 465602Notes

Reaction equation

HRID 465602 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C(N(CC)CC)C.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>ClCCl>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:14][CH2:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 14986702Ethyl 8-amino-4-[3-(3-pyridyl)propyl]-octanoate

Product 1

HCID 10322927Ethyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2200 g or crude ethyl 8-amino-4-[3-(3-pyridyl)propyl]-octanoate in 28.8 l of dichloromethane is added 1377 g of triethylamine. The solution is cooled to 0° and a solution of 1435 g of p-chlorophenylsulfonyl chloride in 14.3 l of dichloromethane is added over a period of 45 min maintaining the temperature below 5°. The reaction mixture is allowed to slowly warm up to room temperature overnight. The reaction mixture is washed 3 times with 15 l of aqueous sodium bicarbonate solution and then with water, dried over sodium sulfate and evaporated to dryness to yield ethyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate (compound of example 4b) as an oil.

Workup

  1. temperatureThe solution is cooled to 0°
  2. temperaturemaintaining the temperature below 5°
  3. washThe reaction mixture is washed 3 times with 15 l of aqueous sodium bicarbonate solution
  4. dry with materialwith water, dried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-3be95c40e0af45fbb07a57593076b6c9
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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